Iridium(iii) catalyzed regioselective amidation of indoles at the C4-position using weak coordinating groups
Veeranjaneyulu Lanke1, Kandikere Ramaiah Prabhu
1Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India. prabhu@orgchem.iisc.ernet.in.
Abstract:
The C4-aminated indole scaffold is frequently encountered in several natural products and biologically active compounds. Herein we disclose a simple and short synthetic route for the amidation of indoles at the C4 position by employing an aldehyde as a directing group and Ir(iii) as a catalyst. This strategy offers high selectivity for the C4-amidation of unprotected and protected indoles. A simple deprotection of the tosyl group leads to the formation of C4-amino indole derivatives, which are useful synthons for synthesizing natural products in the teleocidin family.
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